Cationic active agent and a method for softening a washable textile fabric therewith



United States Patent M F 45, Int. Cl. C21h 1/00; C08j 1/38; D06m 3/02 US. Cl. 117-1395 4 Claims ABSTRACT OF THE DISCLOSURE Cation active compounds of the type exemplified by the formula wherein R and R are individually defined as alkyl radicals of 11-21 carbon atoms; R is hydrogen or methyl;

AGENT AND A METHOD FOR 3,451,844- Patented June 24, 1969 and in fact in the form of dilute, about 510% aqueous solutions or emulsions, in order to ensure their rapid and uniform distribution in this rinsing liquor.

The required amounts of the cation-active compounds can readily be established during preliminary experiments; amounts of 0.1%, referred to the dry weight of the textiles to be treated, are in general already found to be suflicient.

The compounds to be employed according to the invention are distinguished by an unexpectedly more intensive activity compared with the fatty acid esters and fatty acid amides mentioned above, particularly with regard to an improvement in the feel of the textiles.

The following examples serve to illustrate the invention without, however, limiting its scope.

EXAMPLE 1 3 kg. of a textile fabric (towelling) consisting of cotton which had been washed and rinsed about 20 times in an automatic drum washing machine with a commercial detergent based on dodecyl-benzene sulphonate, and which had become stiff and hard after drying, are treated with the cation-active compound of the formula R is an alkyl radical of 1-4 carbon atoms; and n is an by adding 3 g. of this compound, in the form of its 7.5%

integer of 0-2; and a method for softening washable textiles by utilizing said compounds.

It is known that textiles which are repeatedly washed can, after washing and rinsing, be after-treated with cation-active agents in order to improve their properties during their use. The monoor di-esters of fatty acids with triethanolamine and the diamides of fatty acids with triethylene tetramine have been employed as the cationactive agents for this purpose.

According to the present invention, compounds of the formula wherein R and R each individually represent an alkyl radical containing 11 to 21 and preferably 15 to 17 carbon atoms, R is hydrogen or methyl, and R is an alkyl radical containing 1 to 4 carbon atoms, whilst X denotes oxygen, the group -NH or the group NCH and n is a number of 0-2, are particularly suitable as cationactive agents for use in a process of this kind.

The cation-active compounds which can be suitably employed according to the invention may for instance be obtained by heating 1 mole of the compound of the formula with 1 mole of the compound of the formula R -COOH and 1 mole of the formula R COOH at 180 to 190 C. for several hours; in these formulae the symbols R R R and R, as well as X and n have the significance mentioned above.

The cation-active compounds are conveniently employed in the form of their salts with lower organic acids or with inorganic acids, such as formic acid and acetic acid or hydrochloric acid and phosphoric acid. When washing and rinsing of the textiles is carried out in automatic washing machines, it is recommended to add the cation-active compounds or their salts, optionally as a mixture with nonionic surface-active compounds such as polyglycol esters of fat alcohols, to the last rinsing liquor,

aqueous emulsion which also contains 3.8% acetic acid as well as 1% oleyl alcohol polyglycol ether, to the last rinsing liquor during a further washing operation. The fabric which has thus been treated then no longer exhibits hardness or stiffness after drying, but has a pleasant soft feel.

The above mentioned cation-active compound and its emulsion as applied had been prepared by the following method:

143 g. bis-N-(B-aminopropyl)-met'hylamine (1 mole) were treated dropwise at 120 in an atmosphere of nitrogen with 568 g. stearic acid (2 moles), and the mixture was thereafter heated at 180-185 C. for 4 hours, again in an atmosphere of nitrogen, in order to distill off the resultant water, the mixture being maintained under a reduced pressure of 100 mm. Hg during the last two hours, The reaction product was then cooled to 100 C., treated with 10.2 g. acetic anhydride (0.1 mole) in order to combine with any remaining unreacted amine, and kept at 100 C. for another 30 minutes.

75 g. of the resultant cation-active compound were heated to 8 090 C. in a sealed vessel in an atmosphere 'of nitrogen whilst stirring, then treated with 877 g. water and 10 g. of the reaction product of 25 moles ethylene oxide with -1 mole oleyl alcohol and finally stirred at C. for another 10 minutes. The solution was thereafter treated with 38 g. of acetic acid, stirred at 90-95 C. for another 15 minutes, and then cooled as quickly as possible.

EXAMPLE 2 (1 mole) were reacted with a mixture of 256 g. (1 mole) palmitic acid and 284 g. stearic acid (1 mole) as well as with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. Thereafter, 75 g. of the resultant cation-active compound of the formula 4 with 10.2 g. acetic anhydride (0.1 mole) by the method described in Example 1. 75 g. of the cation-active com- CHzCHa EXAMPLE 3 3 kg. of a mixed fabric consisting of polyacrylonitrile fibres and of wool with a shrink-proofing finish, which had been washed and rinsed 20 times in an automatic drum washing machine with a commercial fine detergent based on alkyl sulphates and which had become stiff and hard after drying, are treated with a mixture of equal parts by weight of the cation-active compounds specified in Example 1 and Example 2, by adding 3 g. of this mixture, in the form of its 7.5% aqueous emulsion which had been prepared in accordance with the statements in Example 1 and which also contains 3.8% acetic acid as well as 1% oleyl alcohol polyglycol ether, to the last rinsing liquor during a further washing operation. The fabric which has thus been treated then no longer exhibits hardness or stifiness after drying, but has a full soft feel.

EXAMPLE 4 3 kg. of a mixed fabric consisting of polyester fibres and rayon which had been washed and rinsed 20 times in an automatic washing machine with a commercial detergent based on dodecyl-benzene sulphonate and which had become stiff and hard after drying, are treated with the cation-active compound of the formula pound thus obtained were then stirred with 905 g. water, with 10 g. of the reaction product of 25 moles ethylene oxide with 1 mole oleyl alcohol and with 10 g. 100% formic acid by the method described in Example 1 to form an aqueous emulsion.

We claim:

1. A compound of the formula wherein R and R are individually defined as alkyl radicals of 11-21 carbon atoms; R is hydrogen or methyl; R is an alkyl radical of 14 carbon atoms; and n is an integer of 0-2.

2. A compound of claim 1 wherein R and R are respectively alkyl of 15-17 carbon atoms; R is hydrogen; R is ethyl and n is 1.

3. A method for softening washable textiles comprising contacting the textiles with an active amount of a compound of claim 1.

4. The method of claim 3 wherein the Washable textiles are cotton, polyacrylonitrile, lWOOl, polyester or rayon, and about 1% by weight of active compound is utilized by weight of dry textile.

(1 mole) were reacted with a mixture of 256 g. palmitic acid (1 mole) and 2 84 g. stearic acid (1 mole) as well as References Cited UNITED STATES PATENTS 2,205,042 6/1940 Lenher et al. 11 7-1395 2,243,980 6/1941 Rheiner et al. 260-4045 X 2,496,776 2/1950 Caldwell 117-1395 2,734,830 2/1956 Hagge et a1. 117-47 3,038,820 6/ 1962 Albrecht 260-4045 X 3,095,373 6/1963 Blomfield 117-47 X 3,168,416 2/ 1965 Zech 1l7-l39.5

WILLIAM D. MARTIN, Primary Examiner.

T. G. DAVIS, Assistant Examiner.

US. Cl. X.R. 

